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Solid-phase synthesis of C-terminal azapeptides.

Solid-phase synthesis of C-terminal azapeptides.

Journal of peptide science : an official publication of the European Peptide Society (2014-11-18)

Ngoc-Duc Doan, Jinqiang Zhang, Mariam Traoré, Winnie Kamdem, William D Lubell

ABSTRACT

The solid-phase synthesis of azapeptides possessing a C-terminal aza-residue has been accomplished by a protocol featuring regioselective alkylation of benzhydrylidene-aza-glycinamide and illustrated by the syntheses of [aza-Lys(6)] growth-hormone-releasing peptide-6 analogs.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Fmoc-D-Phe-OH, ≥98.0%

Sigma-Aldrich

Benzophenone hydrazone, 96%

Sigma-Aldrich

Boc-His(Trt)-OH, ≥98.0% (TLC)

Sigma-Aldrich

Hydroxylamine hydrochloride, 99.999% trace metals basis

Sigma-Aldrich

Hydroxylamine hydrochloride, 99.995% trace metals basis

Sigma-Aldrich

N,N′-Disuccinimidyl carbonate, ≥95%

Sigma-Aldrich

Hydroxylamine hydrochloride, JIS special grade, ≥98.0%

Sigma-Aldrich

Pyridine, JIS special grade, ≥99.5%

Sigma-Aldrich

Diethylamine, SAJ special grade, ≥99.0%

Sigma-Aldrich

Diethylamine, SAJ first grade, ≥98.0%

Sigma-Aldrich

Pyridine, ≥99%

Sigma-Aldrich

1-Bromo-4-chlorobutane, 99%

Sigma-Aldrich

Pyridine, anhydrous, 99.8%

Sigma-Aldrich

4-Methylbenzyl bromide, 97%

Sigma-Aldrich

Fmoc-Ala-OH, 95%

Sigma-Aldrich

Fmoc-D-Trp(Boc)-OH, ≥95.0% (HPLC)

Sigma-Aldrich

Diethylamine, puriss. p.a., ≥99.5% (GC)

Sigma-Aldrich

N,N-Diisopropylethylamine, ReagentPlus^®, ≥99%

Sigma-Aldrich

Diethylamine, ≥99.5%

Sigma-Aldrich

N,N-Diisopropylethylamine, purified by redistillation, 99.5%

Sigma-Aldrich

Diethylamine, purified by redistillation, 99.5%

Sigma-Aldrich

Pyridine, suitable for hydroxyl value determination, ≥99.5%